Abstract
An efficient and versatile synthesis of the naturally occurring C-prenylated stilbenoid methyl ethers and their synthetic analogues is presented. The synthesis represents a six step convergent process including an optimised C-prenylation method. Furthermore, during the demethylation process, six new dihydro-benzopyranyl derivatives were obtained and isolated.
Highlights
All of the stilbenoids contain a 1,2-diphenylethylene skeleton. They belong to a family of plant phenolics known for their structural complexity and diverse biological activities
In order to obtain C-prenylated stilbenoids rst, we studied the reaction of resveratrol methyl ether with n-BuLi so-called ortholithiation followed by the addition of prenyl bromide
Three of them are entirely new compounds. This convergent process comprises of usually six steps, including an optimised prenylation procedure and condensation reaction
Summary
Stilbenoids are hydroxylated derivatives of stilbene and are a well-known class of naturally occurring phytochemicals. All of the stilbenoids contain a 1,2-diphenylethylene skeleton. They belong to a family of plant phenolics known for their structural complexity and diverse biological activities. They occur with a limited but heterogeneous distribution in plants.[1]. These compounds are stress metabolites produced in leaves and sapwood in response to pathogen infection.[2,3]. They play a crucial role as plant defence compounds, they possess high diversity of impacts on cellular and biological mechanisms affecting human health These compounds are stress metabolites produced in leaves and sapwood in response to pathogen infection.[2,3] they play a crucial role as plant defence compounds, they possess high diversity of impacts on cellular and biological mechanisms affecting human health
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